Hydrochloric Acid → 4-{[3-(Trimethoxysilyl)propyl]thio}-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone

HRID 732854

Reaction equation

HRID 732854 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12]([CH3:14])=[O:13].[SH:15][CH2:16][CH2:17][CH2:18][Si:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21].Cl>C1CCN2C(=NCCC2)CC1>[CH3:21][O:20][Si:19]([O:22][CH3:23])([O:24][CH3:25])[CH2:18][CH2:17][CH2:16][S:15][CH:10]([C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])[CH2:11][C:12](=[O:13])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20473(3-Mercaptopropyl)trimethoxysilaneHCID 638014I2-Ionone

Product 1

HCID 688178914-{[3-(Trimethoxysilyl)propyl]thio}-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanoneYield 88.9%

Reagents, catalysts & solvents 1

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalyst

Procedure

To a well-stirred mixture of β-ionone (10.00 g, 52.1 mmol) and DBU (79 mg, 0.52 mmol (1 mol-%)) was rapidly added 3-mercaptopropyltrimethoxysilane (10.21 g, 52.1 mmol) at 25-30° C. After 72 hours, the reaction mixture was poured onto a cold stirred 5% aqueous HCl solution and extracted twice with Et2O. The organic phases were washed (H2O, saturated aqueous NaHCO3 and brine), dried (Na2SO4), filtered and concentrated. The crude extract was dried for 1 hour at 65-70° C./0.01 Torr to give 18.00 g of the title thioether containing approximativaly 10% of β-ionone. Yield: 80%.

Workup

  1. customat 25-30° C
  2. additionthe reaction mixture was poured onto
  3. extractionextracted twice with Et2O
  4. washThe organic phases were washed (H2O, saturated aqueous NaHCO3 and brine)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. extractionThe crude extract
  9. customwas dried for 1 hour at 65-70° C./0.01 Torr

Sources & evidence

ORD record
ord-f419cbac44c6454b93d26078fa5db95a
Source dataset
uspto-grants-2009_09
Patent number
US07589055B2

Linked notes

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